Piperine

Last updated
Piperine
Piperin.svg
Piperine crystals.jpg
Names
Preferred IUPAC name
(2E,4E)-5-(2H-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Other names
(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Piperoylpiperidine
Bioperine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.135 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+ X mark.svgN
    Key: MXXWOMGUGJBKIW-YPCIICBESA-N X mark.svgN
  • InChI=1/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
    Key: MXXWOMGUGJBKIW-YPCIICBEBY
  • O=C(N1CCCCC1)\C=C\C=C\c2ccc3OCOc3c2
Properties
C17H19NO3
Molar mass 285.343 g·mol−1
Density 1.193 g/cm3
Melting point 130 °C (266 °F; 403 K)
Boiling point Decomposes
40 mg/l
Solubility in ethanol soluble
Solubility in chloroform 1 g/1.7 ml
Hazards
Safety data sheet (SDS) MSDS for piperine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Piperine
Scoville scale 150,000 [1] SHU

Piperine, possibly along with its isomer chavicine, [2] is the compound [3] responsible for the pungency of black pepper and long pepper. It has been used in some forms of traditional medicine. [4]

Contents

Preparation

Due to its poor solubility in water, piperine is typically extracted from black pepper by using organic solvents like dichloromethane. [5] The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers. [6] [7]

Piperine can also be prepared by treating the solvent-free residue from a concentrated alcoholic extract of black pepper with a solution of potassium hydroxide to remove resin (said to contain chavicine, an isomer of piperine). [7] The solution is decanted from the insoluble residue and left to stand overnight in alcohol. During this period, the alkaloid slowly crystallizes from the solution. [8]

Piperine has been synthesized by the action of piperonoyl chloride on piperidine. [7]

Reactions

Piperine forms salts only with strong acids. The platinichloride B4·H2PtCl6 forms orange-red needles ("B" denotes one mole of the alkaloid base in this and the following formula). Iodine in potassium iodide added to an alcoholic solution of the base in the presence of a little hydrochloric acid gives a characteristic periodide, B2·HI·I2, crystallizing in steel-blue needles with melting point 145 °C. [7]

Piperine can be hydrolyzed by an alkali into piperidine and piperic acid. [7]

In light, especially ultra-violet light, piperine is changed into its isomers chavicine, isochavicine and isopiperine, which are tasteless. [9] [2]

History

Piperine was discovered in 1819 by Hans Christian Ørsted, who isolated it from the fruits of Piper nigrum , the source plant of both black and white pepper. [10] Piperine was also found in Piper longum and Piper officinarum (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper". [11]

Biochemistry and medicinal aspects

A component of pungency by piperine results from activation of the heat- and acidity-sensing transient receptor potential channel ion channels, TRPV1 and TRPA1, on nociceptors, the pain-sensing nerve cells. [12] Piperine is under preliminary research for its potential to affect bioavailability of other compounds in food and dietary supplements, such as a possible effect on the bioavailability of curcumin. [13]

See also

Related Research Articles

<i>Piper</i> (plant) Genus of plants

Piper, the pepper plants or pepper vines, is an economically and ecologically important genus in the family Piperaceae.

<span class="mw-page-title-main">Piperidine</span> Chemical compound

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines. The name comes from the genus name Piper, which is the Latin word for pepper. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a chemical irritant and neurotoxin for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, probably as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent, crystalline to waxy solid compound.

<span class="mw-page-title-main">Black pepper</span> Ground fruit of the family Piperaceae

Black pepper is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about 5 mm (0.20 in) in diameter, dark red, and contains a stone which encloses a single pepper seed. Peppercorns and the ground pepper derived from them may be described simply as pepper, or more precisely as black pepper, green pepper, or white pepper.

A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

<span class="mw-page-title-main">Coniine</span> Chemical compound

Coniine is a poisonous chemical compound, an alkaloid present in and isolable from poison hemlock (Conium maculatum), where its presence has been a source of significant economic, medical, and historico-cultural interest; coniine is also produced by the yellow pitcher plant (Sarracenia flava), and fool's parsley (Aethusa cynapium). Its ingestion and extended exposure are toxic to humans and all classes of livestock; its mechanism of poisoning involves disruption of the central nervous system, with death caused by respiratory paralysis. The biosynthesis of coniine contains as its penultimate step the non-enzymatic cyclisation of 5-oxooctylamine to γ-coniceine, a Schiff base differing from coniine only by its carbon-nitrogen double bond in the ring. This pathway results in natural coniine that is a mixture—a racemate—composed of two enantiomers, the stereoisomers (S)-(+)-coniine and (R)-(−)-coniine, depending on the direction taken by the chain that branches from the ring. Both enantiomers are toxic, with the (R)-enantiomer being the more biologically active and toxic of the two in general. Coniine holds a place in organic chemistry history as being the first of the important class of alkaloids to be synthesized, by Albert Ladenburg in 1886, and it has been synthesized in the laboratory in a number of unique ways through to modern times.

<span class="mw-page-title-main">Piperazine</span> Chemical compound

Piperazine is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste.

<span class="mw-page-title-main">Allyl isothiocyanate</span> Chemical compound

Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of Cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels. It is slightly soluble in water, but more soluble in most organic solvents.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Crotonic acid</span> Chemical compound

Crotonic acid ((2E)-but-2-enoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. It is called crotonic acid because it was erroneously thought to be a saponification product of croton oil. It crystallizes as colorless needles from hot water. With a cis-alkene, Isocrotonic acid is an isomer of crotonic acid. Crotonic acid is soluble in water and many organic solvents. Its odor is similar to that of butyric acid.

<span class="mw-page-title-main">Long pepper</span> Species of plant cultivated for its fruit which is used as a spice

Long pepper, sometimes called Indian long pepper or pippali, is a flowering vine in the family Piperaceae, cultivated for its fruit, which is usually dried and used as a spice and seasoning. Long pepper has a taste similar to, but sweeter and less pungent than, that of its close relative Piper nigrum – from which black, green and white pepper are obtained.

<span class="mw-page-title-main">Arecoline</span> Mild stimulant

Arecoline is a nicotinic acid-based mild parasympathomimetic stimulant alkaloid found in the areca nut, the fruit of the areca palm. It is an odourless oily liquid. It can bring a sense of enhanced alertness and energy, euphoria and relaxation. The psychoactive effects are comparable to that of nicotine.

<i>Piper guineense</i> Species of flowering plant

Piper guineense is a West African species of Piper; the spice derived from its dried fruit is known as Ashanti pepper, Benin pepper, Edo pepper, false cubeb, Guinea cubeb, and called locally kale, kukauabe, masoro, etiñkeni, sasema, soro wisa, eyendo, eshasha by the Urhobo people, and oziza and uziza by the Igbo people of Nigeria. It is a close relative of cubeb pepper and a relative of black pepper and long pepper. Unlike cubeb, which is large and spherical in shape, Ashanti pepper grains are prolate spheroids, smaller and smoother than Cubeb pepper in appearance and generally bear a reddish tinge. The stalks of Ashanti pepper berries are also distinctly curved whilst those of cubeb pepper are completely straight. The terms West African pepper and Guinea pepper have also been used, but are ambiguous and may refer to grains of Selim or grains of paradise.

Nonivamide, also called pelargonic acid vanillylamide or PAVA, is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. It is more heat-stable than capsaicin.

<span class="mw-page-title-main">Chavicine</span> Chemical compound

Chavicine is possibly pungent compound found in black pepper and other species of the genus Piper. It is one of the four geometric isomers of piperine.

<span class="mw-page-title-main">Ilepcimide</span> Chemical compound

Ilepcimide, also known as antiepilepserine, is an anticonvulsant. It is a piperidine derivative that was first synthesized by Chinese researchers as an analogue of piperine, the main pungent compound and phytochemical of black pepper.

<span class="mw-page-title-main">Pungency</span> Sharp smell or flavor

Pungency refers to the taste of food commonly referred to as spiciness, hotness or heat, found in foods such as chili peppers. Highly pungent tastes may be experienced as unpleasant. The term piquancy is sometimes applied to foods with a lower degree of pungency that are "agreeably stimulating to the palate". Examples of piquant food include mustard and curry.

<span class="mw-page-title-main">Piperic acid</span> Chemical compound

Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine from black pepper, followed by acidification of the corresponding salt. Piperic acid is an intermediate in the synthesis of other compounds such as piperonal, and as-such may be used to produce fragrances, perfumes flavorants and drugs as well as other useful compounds.

<span class="mw-page-title-main">Bioenhancer</span> Substances which increase efficacy of drugs

Bioenhancers or biopotentiators or bioavailability enhancers is a new chapter in medical science first scientifically established in 1979 after the discovery of world's first bioenhancer piperine. It is a pocket friendly drug technology which reduces the destruction, wastage and elimination of several orally administered drugs inside the body.

<span class="mw-page-title-main">Piperidine alkaloids</span>

Piperidine alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from piperidine.

References

  1. Mangathayaru, K. (2013). Pharmacognosy: An Indian perspective. Pearson Education India. p. 274. ISBN   9789332520264.
  2. 1 2 De Cleyn, R; Verzele, M (1972). "Constituents of peppers. I Qualitative Analysis of Piperine Isomers" (PDF). Chromatografia. 5: 346–350. doi:10.1007/BF02315254. S2CID   56022338 . Retrieved 26 September 2023.
  3. The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, p. 7442, ISBN   091191028X
  4. Srinivasan, K. (2007). "Black pepper and its pungent principle-piperine: A review of diverse physiological effects". Critical Reviews in Food Science and Nutrition. 47 (8): 735–748. doi:10.1080/10408390601062054. PMID   17987447. S2CID   42908718.
  5. Epstein, William W.; Netz, David F.; Seidel, Jimmy L. (1993). "Isolation of Piperine from Black Pepper". J. Chem. Educ. 70 (7): 598. Bibcode:1993JChEd..70..598E. doi:10.1021/ed070p598.
  6. "Pepper". Tis-gdv.de. Retrieved 2 September 2017.
  7. 1 2 3 4 5 Henry, Thomas Anderson (1949). "Piperine". The Plant Alkaloids (4th ed.). The Blakiston Company. p. 1-2.
  8. Ikan, Raphael (1991). Natural Products: A Laboratory Guide (2nd ed.). San Diego, CA: Academic Press. pp. 223–224. ISBN   0123705517.
  9. Kozukue, Nobuyuki; Park, Mal-Sun; others, and 5 (2007). "Kinetics of Light-Induced Cis−Trans Isomerization of Four Piperines and Their Levels in Ground Black Peppers as Determined by HPLC and LC/MS". J. Agric. Food Chem. 55 (17): 7131–7139. doi:10.1021/jf070831p. PMID   17661483 . Retrieved 26 September 2023.
  10. Ørsted, Hans Christian (1820). "Über das Piperin, ein neues Pflanzenalkaloid" [On piperine, a new plant alkaloid]. Schweiggers Journal für Chemie und Physik (in German). 29 (1): 80–82.
  11. Friedrich A. Fluckiger; Daniel Hanbury (1879). Pharmacographia : a History of the Principal Drugs of Vegetable Origin, Met with in Great Britain and British India. London: Macmillan. p.  584. ASIN   B00432KEP2.
  12. McNamara, F. N.; Randall, A.; Gunthorpe, M. J. (March 2005). "Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1)". British Journal of Pharmacology. 144 (6): 781–790. doi:10.1038/sj.bjp.0706040. PMC   1576058 . PMID   15685214.
  13. Kunnumakkara, A. B.; Bordoloi, D.; Padmavathi, G.; Monisha, J.; Roy, N. K.; Prasad, S.; Aggarwal, B. B. (2017). "Curcumin, the Golden Nutraceutical: Multitargeting for Multiple Chronic Diseases". British Journal of Pharmacology. 174 (11): 1325–1348. doi: 10.1111/bph.13621 . PMC   5429333 . PMID   27638428.